Can you be too old to be forever young? It’s a particularly relevant question right now for Paul Reubens, who at 59 is showing his age even behind the thick pancake makeup of his signature character Pee-Wee Herman. Of course the whole conceit of Pee-Wee, from the very beginning, has been that he’s trapped in a state of arrested development, cartoonishly innocent in a way that’s both charming and unsettling. Pee-Wee is a character seemingly custom-built to wear for a lifetime—but no man can live forever, and Reubens’s recent resurgence is strangely poignant.

Reubens is not the first entertainer of a certain age to find himself irrevocably associated—for better and for worse—with a project he couldn’t have initially guessed would come to define his life. Pee-Wee was born in the 70s, when Reubens was working on the improv and sketch comedy scene in Los Angeles. Reubens developed a live show around the character, capitalizing from the beginning on Pee-Wee’s appeal to both children and adults: he’d perform matinees for kids and midnight shows for adults. Pee-Wee rose to worldwide fame in the 80s, starting with an HBO spotlight in 1981 and continuing on to a national tour, the 1985 hit movie Pee-Wee’s Big Adventure, and the 1986 debut of his TV show Pee-Wee’s Playhouse.

At first, Pee-Wee’s multigenerational appeal was both perfectly post-modern and timelessly savvy: the idea of an entertainment that has a simple appeal for children and an added layer of meaning for adults is as old as Homer. But Reubens took his newfound role as an educator seriously, and over his acclaimed show’s four-year run, Pee-Wee became increasingly considered to be primarily a children’s character.

By 1991, Reubens was already on hiatus from Pee-Wee: he hadn’t been in character for a year and a half when he was arrested for indecent exposure in a darkened, but public, porno house. If Pee-Wee had been a complicated sort of role model before, he certainly was after that, and the culture-warring 90s was no time to be a scandalized children’s entertainer. After a triumphantly self-deprecating appearance at the 1991 MTV Video Music Awards (receiving a standing ovation, he asked, “Heard any good jokes lately?” and followed up with his trademark catchphrase, “That’s so funny I forgot to laugh!”), Reubens hung up his skinny suit and waited out the storm.

Pee-Wee seemed to have passed the point of no return when Reubens was again arrested, in 2002, for possessing a large collection of erotica that included material characterized by the authorities as child pornography—Reubens acknowledged the material contained depictions of underage nudes, but insisted it was art photography and denied being “titillated” by images of children—but the kids who grew up watching Pee-Wee’s Playhouse are no longer living with their parents, and in the past few years Pee-Wee has returned to the public eye in a surprisingly big way, with multiple appearances on national TV and a Broadway run of The Pee-Wee Herman Show.

The character’s comeback has been fueled by a savvy social media team who’ve helped Reubens capitalize on the appeal of Pee-Wee in the meme-riding, retro-ready Internet culture of the 21st century—but it’s hard not to have mixed emotions about Pee-Wee 2k12. On the one hand, Pee-Wee’s return to glory is an inspiring comeback story and a well-deserved apology from a culture that cruelly pilloried Reubens 20 years ago. On the other hand, Reubens is having a hard time selling Pee-Wee to kids born while he was on hiatus. The Broadway show sold well, but earned mixed reviews: in The New Yorker, John Lahr criticized the show as joyless and called it “the comic equivalent of lint.” New film projects much-discussed by Reubens/Pee-Wee over the past decade have failed to come to fruition.

The irony of Pee-Wee at 60 is that acting young, for Reubens, is acting old. The days when Pee-Wee rode highest on the seat of his red bicycle were the days now being treated historically in shows like Rock of Ages (to say nothing of Rock of Love). Pee-Wee’s mock nostalgia act felt fresh and subversive in the 80s; now, it’s a genuine nostalgia act.

What does it mean to be young, really? It doesn’t mean romping around in a playhouse any more than it means being relevant on Foursquare: it means growing, and taking risks. Bob Dylan gets it: his bizarre Christmas album and accompanying videos confused, fascinated, and amused. Whether you love him or hate him, Dylan demonstrates that never letting yourself get bored with yourself is the best way to remain interesting to audiences of all ages. As for Pee-Wee, he’s back and that’s cool—but those little kids he’s looking to impress are getting up and falling on their faces every day. If he really wants to be forever young, Pee-Wee Herman—like any of us—is going to have to be willing to do the same.

– Jay Gabler